iodine; magnesium 1.) THF, reflux, 30 min, 2.) THF, reflux, 2 h; Yield given. Multistep reaction;

anhydrous butyl ether

1: 50 percent / sulfuric acid, H2O / 1.5 h / 100 °C 2: 99 percent / benzene; diethyl ether / 16 h / Heating 3: TiCl3, LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 83 percent / Fermy's salt, KH2PO4, H2O / benzene / 0.5 h View Scheme

1: 50 percent / sulfuric acid, H2O / 1.5 h / 100 °C 2: 99 percent / benzene; diethyl ether / 16 h / Heating 3: TiCl3, LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 83 percent / Fermy's salt, KH2PO4, H2O / benzene / 0.5 h 5: 94 percent / NaBH4, O2 / ethanol / 72 h 6: m-chlorobenzoic acid / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: 50 percent / sulfuric acid, H2O / 1.5 h / 100 °C 2: 99 percent / benzene; diethyl ether / 16 h / Heating 3: TiCl3, LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 83 percent / Fermy's salt, KH2PO4, H2O / benzene / 0.5 h 5: 94 percent / NaBH4, O2 / ethanol / 72 h View Scheme

sodium hydroxide; zinc Heating;

1: 50 percent / sulfuric acid, H2O / 1.5 h / 100 °C 2: 99 percent / benzene; diethyl ether / 16 h / Heating 3: TiCl3, LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

methanesulfonic acid T=100°C; 1.5 h;